How about the Berkshires in western Mass. (say around Lenox):
These attractions would be
For culture/dining:
Norman Rockwell Museum
Williams College Museum
Tanglewood Festival
Glimmerglass Opera (Cooperstown - 2 hours they have matinees)
Sports:
Baseball Hall of Fame (Cooperstown NY - 2 hours)
Basketball Hall of Fame (Springfield Mass)
Gambling:
Indian Casinos in Connecticut
Outdoors recreation and scenery is unlimited.
Also when you head up to Canada, if you go near Waterbury, Vermont, stop at the Ben abd Jerry's factory for a tour